Jeff McCombs - 18 May 2022 Form 4 Insider Report for UPWORK, INC (UPWK)

Role: Chief Financial Officer
Signature: /s/ Jacob McQuown, Attorney-in-Fact
Issuer symbol: UPWK
Transactions as of: 18 May 2022
Net transactions value: -$56,363
Form type: 4
Filing time: 20 May 2022, 19:04:36 UTC
Previous filing: 24 Feb 2022
Next filing: 22 Aug 2022
SEC: View on sec.gov

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	UPWK	Common Stock	Options Exercise		+732	+9.6%		8,330	18 May 2022	Direct	F1, F2
transaction	UPWK	Common Stock	Options Exercise		+1,472	+18%		9,802	18 May 2022	Direct	F1
transaction	UPWK	Common Stock	Options Exercise		+7,134	+73%		16,936	18 May 2022	Direct	F1
transaction	UPWK	Common Stock	Sale	$56,363	-3,508	-21%	$16.07	13,428	18 May 2022	Direct	F3, F4

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	UPWK	Restricted Stock Units (RSU)	Options Exercise	$0	-732	-8.3%	$0.000000	8,056	18 May 2022	Common Stock	732		Direct	F1, F5
transaction	UPWK	Restricted Stock Units (RSU)	Options Exercise	$0	-1,472	-8.3%	$0.000000	16,190	18 May 2022	Common Stock	1,472		Direct	F1, F6
transaction	UPWK	Restricted Stock Units (RSU)	Options Exercise	$0	-7,134	-6.2%	$0.000000	107,021	18 May 2022	Common Stock	7,134		Direct	F1, F7

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.
F2	Includes 810 shares acquired under the Issuer's employee stock purchase plan on May 13, 2022.
F3	Represents the number of shares required to be sold by the Reporting Person to cover tax withholding obligations in connection with the vesting of the RSUs listed in Table II. This sale is mandated by the Issuer's election under its equity incentive plans to require the satisfaction of tax withholding obligations to be funded by a "sell to cover" transaction and does not represent a discretionary trade by the Reporting Person.
F4	The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $15.94 to $16.31 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon written request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.
F5	The RSUs vest 25% on February 18, 2022, and then 6.25% of the total shares vest on each quarterly anniversary thereafter, subject to the Reporting Person's continued employment with the Issuer on each vesting date.
F6	The RSUs vest in equal quarterly installments over four years beginning on May 18, 2021, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.
F7	The RSUs vest in equal quarterly installments over four years beginning on May 18, 2022, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.